Patents Represented by Attorney James Arno

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  • Intermediate for the preparation of thienamycin
    Patent number: 4344885
    Abstract: Disclosed is a process for the stereocontrolled total synthesis of thienamycin from acetone dicarboxylate via intermediate II: ##STR1## wherein R is a readily removable carboxyl protecting group.
    Type: Grant
    Filed: April 17, 1981
    Date of Patent: August 17, 1982
    Assignee: Merck & Co., Inc.
    Inventors: Thomas M. H. Liu, David G. Melillo, Kenneth M. Ryan, Ichiro Shinkai, Meyer Sletzinger
  • Process for the preparation of carbapenem antibiotics
    Patent number: 4341706
    Abstract: Disclosed is a process for the synthesis of carbapenem antibiotics I and their pharmaceutically acceptable salts and esters from 1: ##STR1## wherein: R.sup.7, R.sup.6, R.sup.1, R.sup.2 and R.sup.8 are selected from hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, spirocycloalkyl, cycloalkylalkyl, alkylcycloalkyl, aryl, aralkyl, aralkenyl, aralkynyl, heteroalkyl, heteroaralkyl, heterocyclyl and heterocyclyalkyl.
    Type: Grant
    Filed: October 10, 1980
    Date of Patent: July 27, 1982
    Assignee: Merck & Co., Inc.
    Inventors: Burton G. Christensen, David H. Shih
  • Thienamycin derivatives
    Patent number: 4341705
    Abstract: Disclosed is a process for the total synthesis of thienamycin from descysteaminylthinamycin 1 ##STR1## via thienamycin sulfoxide 4: ##STR2## R.sup.3, R.degree., R' are blocking groups.
    Type: Grant
    Filed: October 10, 1980
    Date of Patent: July 27, 1982
    Assignee: Merck & Co., Inc.
    Inventor: David H. Shih
  • 6-, 2- and 1,1-Disubstituted-1-carbadethiapen-2-em-3-carboxylic acid S-oxides
    Patent number: 4341791
    Abstract: Disclosed are S-oxides of 6-, 2- and 1,1-disubstituted-1-carbadethiapen-2-em-3-carboxylic acids having the structure: ##STR1## wherein: n is 1 or 2; and R.sup.1, R.sup.2, R.sup.6, R.sup.7 and R.sup.8 are, inter alia, independently selected from the group consisting of hydrogen, alkyl, alkenyl, aryl and aralkyl. Such compounds as well as their pharmaceutically acceptable salt, ester and amide derivatives are useful as antibiotics. Also disclosed are processes for the preparation of such compounds, pharmaceutical compositions comprising such compounds and methods of treatment comprising administering such compounds and compositions when an antibiotic effect is indicated.
    Type: Grant
    Filed: October 10, 1980
    Date of Patent: July 27, 1982
    Assignee: Merck & Co., Inc.
    Inventors: Burton G. Christensen, David H. Shih
  • Fermentation process for (5R,6S,8S)-3-(2-aminoethylthio)-6-(1-hydroxyethyl)-7-oxo-1-azabicyclo[3. 2.0]hept-2-ene-2-carboxylic acid
    Patent number: 4335212
    Abstract: Disclosed is a fermentation process for preparing and isolating the antibiotic, (5R,6S,8S)-3-(2-aminoethylthio)-6-(1-hydroxyethyl)-7-oxo-1-azabicyclo[3.2. 0]hept-2-ene-2-carboxylic acid in substantially pure form.
    Type: Grant
    Filed: June 17, 1981
    Date of Patent: June 15, 1982
    Assignee: Merck & Co., Inc.
    Inventors: Kenneth E. Wilson, August J. Kempf
  • Process for the preparation of N-protected N-formimidoyl 2-aminoethanethiol
    Patent number: 4329481
    Abstract: Disclosed is 2 and a process for its preparation: ##STR1## It is useful in the synthesis of N-formimidoyl thienamycin; R.sup.2 is hydrogen or a protecting group.
    Type: Grant
    Filed: April 17, 1981
    Date of Patent: May 11, 1982
    Assignee: Merck & Co., Inc.
    Inventors: Thomas M. H. Liu, Robert A. Reamer, Ichiro Shinkai, Meyer Sletzinger
  • 3-Amino-4-C-carboxy-2,3,4,6-tetradeoxy-D-arabino-hexose trimethylene dithioacetal
    Patent number: 4324900
    Abstract: Disclosed is a chiral, total synthesis of thienamycin from D-glucose, which proceeds via intermediates I, II, and III and joins aldehyde IV or acid V, which are known to be useful in the total synthesis of thienamycin (VI): ##STR1## wherein R.sup.1 is hydrogen or a removable protecting group;R is lower alkyl having 1-6 carbon atoms or bi-valent alkyl having 2-6 carbon atoms which joins the two sulfur atoms.
    Type: Grant
    Filed: March 30, 1981
    Date of Patent: April 13, 1982
    Assignee: Merck & Co., Inc.
    Inventor: Philippe L. Durette
  • 6-(1-Hydroxyethyl)-3-substituted-1-azabicyclo(3.2.0)-hept-2-en-7-one-2-ca rboxylic acid
    Patent number: 4318912
    Abstract: Disclosed are 6-(1'-hydroxyethyl)-3-substituted-1-azabicyclo[3.2.0]hept-2-en-7-one-2-car boxylic acids(I): ##STR1## wherein X is halo, oxygen (the 2-3 bond is saturated and the species I exists as the carboxylate salt or ester), or --OR wherein R is, inter alia, acyl, alkyl or aralkyl. Such compounds and their O- and carboxyl derivatives are useful as antibiotics. Also disclosed are processes for the preparation of such compounds, pharmaceutical compositions comprising such compounds and methods of treatment comprising administering such compounds and compositions when an antibiotic effect is indicated.
    Type: Grant
    Filed: June 18, 1980
    Date of Patent: March 9, 1982
    Assignee: Merck & Co., Inc.
    Inventors: Burton G. Christensen, Ronald W. Ratcliffe
  • 6-, 1- And 2-substituted-1-carbadethiapen-2-em-3-carboxylic acids
    Patent number: 4312871
    Abstract: Disclosed are 6-, 1- and 2-substituted-1-carbadethiapen-2-em-3-carboxylic acids having the structure: ##STR1## wherein: R.sup.1, R.sup.2, R.sup.6, R.sup.7 and R.sup.8 are, inter alia, independently selected from the group consisting of hydrogen, alkyl, alkenyl, aryl and aralkyl. Such compounds as well as their pharmaceutically acceptable salt, ester and amide derivatives are useful as antibiotics. Also disclosed are processes for the preparation of such compounds, pharmaceutical compositions comprising such compounds and methods of treatment comprising administering such compounds and compositions when an antibiotic effect is indicated.
    Type: Grant
    Filed: December 3, 1979
    Date of Patent: January 26, 1982
    Assignee: Merck & Co., Inc.
    Inventors: Burton G. Christensen, David H. Shih
  • Substituted N-methylene derivatives of thienamycin
    Patent number: 4311704
    Abstract: Disclosed are substituted N-methylene derivatives of thienamycin having the formula: ##STR1## wherein: (1.) X.dbd.--NR.sup.1 R.sup.2, and Y.dbd.--R'--N.dbd.CRNR.sup.1 R.sup.2, and(2.) X.dbd.R, and Y.dbd.--NR.sup.1 R'N.dbd.CRNR.sup.1 R.sup.2 ; andwherein: R is, inter alia, hydrogen, NH.sub.2, --NHR.sup.1, --NR.sup.1 R.sup.2, R.sup.1 and R.sup.2 ; R.sup.1 and R.sup.2 are independently selected from: hydrogen, substituted, or unsubstituted: alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, aralkyl, heteroaryl, heteroaralkyl, heterocyclyl, and heterocyclylalkyl; R' is --(CH.sub.2).sub.n.sup.-, n is 1-6, or --(CH.sub.2).sub.m --Q--(CH.sub.2).sub.p.sup.-, m, n.dbd.1-3 and Q is O, S or R' is a carbocyclic or heterocyclic ring. Such compounds and their pharmaceutically acceptable salt, ether, ester and amide derivatives are useful as antibiotics.
    Type: Grant
    Filed: June 16, 1980
    Date of Patent: January 19, 1982
    Assignee: Merck & Co., Inc.
    Inventors: Burton G. Christensen, William J. Leanza, David H. Shih, Kenneth J. Wildonger
  • 3-Halo-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylic acid
    Patent number: 4310538
    Abstract: Disclosed is 3-halo-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylic acid (I): ##STR1## Such compounds, wherein X is halo, and their pharmaceutically acceptable salt, ester and amide derivatives are useful as antibiotics. Also disclosed are processes for the preparation of such compounds, pharmaceutical compositions comprising such compounds and methods of treatment comprising administering such compounds and compositions when an antibiotic effect is indicated.
    Type: Grant
    Filed: May 23, 1980
    Date of Patent: January 12, 1982
    Assignee: Merck & Co., Inc.
    Inventors: Burton G. Christensen, Ronald W. Ratcliffe
  • Process for the preparation of 1-carbapenems and intermediates via trithioorthoacetates
    Patent number: 4309346
    Abstract: Disclosed is a process for the total synthesis of 1-carbapenem antibiotics (I) from L-aspartic acid via intermediates II and III: ##STR1## wherein R is hydrogen, a pharmaceutically acceptable ester moiety or salt cation, or a readily removable blocking group; R.sup.6 and R.sup.7 are, inter alia, independently selected from the group consisting of hydrogen, alkyl, alkenyl, aryl and aralkyl; R.sup.1' is hydrogen or a protecting group; and R.sup.a, R.sup.b and R.sup.c are independently selected from alkyl, aryl and aralkyl.
    Type: Grant
    Filed: March 27, 1980
    Date of Patent: January 5, 1982
    Assignee: Merck & Co., Inc.
    Inventors: Burton G. Christensen, Ronald W. Ratcliffe, Thomas N. Salzmann
  • N-Alkyl-N-iminomethyl derivatives of thienamycin
    Patent number: 4309438
    Abstract: Disclosed are N-alkyl-N-iminomethyl derivatives of thienamycin which may be represented by the following structural formula: ##STR1## wherein R.sup.5 is, inter alia, alkyl, alkenyl, aryl, or aralkyl, R.sup.6 is selected from R, OR, SR and NR.sup.1 R.sup.2 wherein R is, inter alia, hydrogen and substituted or unsubstituted: alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, aralkyl, heteroaryl, heteroaralkyl, heterocyclyl, and heterocyclylalkyl; and R.sup.1 and R.sup.2 are hydrogen or R. Such compounds, including their O-- and carboxyl derivatives are useful as antibiotics. Also dislosed are processes for the preparation of such compounds: pharmaceutical compositions comprising such compounds; and methods of treatment comprising administering such compounds and compositions when an antibiotic effect is indicated.
    Type: Grant
    Filed: March 31, 1980
    Date of Patent: January 5, 1982
    Assignee: Merck & Co., Inc.
    Inventors: Burton G. Christensen, William J. Leanza, Kenneth J. Wildonger
  • 6-(1'-Hydroxyethyl)-2-substituted-pen-2-em-3-carboxylic acid
    Patent number: 4301074
    Abstract: Disclosed are 6-(1'-hydroxyethyl)-2-substituted-pen-2-em-3-carboxylic acids of the following structure: ##STR1## wherein R is, inter alia, hydrogen, --OR, --SR, --NR.sub.2, alkyl, aryl, aralkyl, or heterocylcyl; n is 0 or 1; when n=1 R is as defined but not --SR. Such compounds and their pharmaceutically acceptable salt and ester derivatives are useful as antibiotics. Also disclosed are processes for the preparation of such compounds, pharmaceutical compositions comprising such compounds and methods of treatment comprising administering such compounds and compositions when an antibiotic effect is indicated.
    Type: Grant
    Filed: December 31, 1979
    Date of Patent: November 17, 1981
    Assignee: Merck & Co., Inc.
    Inventors: Burton G. Christensen, Frank P. DiNinno
  • Process for preparing N-protected 2-aminoethanethiol
    Patent number: 4299974
    Abstract: Disclosed is a process for preparing N-protected 2-aminoethanethiol which proceeds via the silyl covered sulfur intermediate: ##STR1## wherein R.sup.1 is triorganosilyl and R.sup.2 is a readily removable N-protecting group.
    Type: Grant
    Filed: June 16, 1980
    Date of Patent: November 10, 1981
    Assignee: Merck & Co., Inc.
    Inventors: Thomas M. H. Liu, Ichiro Shinkai, Meyer Sletzinger
  • 6-Amido-3-substituted-1-azabicyclo[3.2.0]-hept-2-en-7-one-2-carboxylic acid
    Patent number: 4298741
    Abstract: Disclosed are 6-amido-3-substituted-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylic acids (I): ##STR1## wherein R.sup.1 is hydrogen or acyl; andX is halo, oxygen (the 2-3 bond is saturated and the species I exists as a carboxylate salt or ester), or --OR wherein R is, inter alia, acyl, alkyl, or aralkyl. Such compounds and their pharmaceutically acceptable salt, ester and amide derivatives are useful as antibiotics. Also disclosed are processes for the preparation of such compounds, pharmaceutical compositions comprising such compounds and methods of treatment comprising administering such compounds and compositions when an antibiotic effect is indicated.
    Type: Grant
    Filed: July 11, 1980
    Date of Patent: November 3, 1981
    Assignee: Merck & Co., Inc.
    Inventors: Burton G. Christensen, Ravindra N. Guthikonda, Ronald W. Ratcliffe
  • Process for the preparation of N-protected N-formimidoyl 2-aminoethanethiol
    Patent number: 4292436
    Abstract: Disclosed is 2 and a process for its preparation: ##STR1## It is useful in the synthesis of N-formimidoyl thienamycin; R.sup.2 is hydrogen or a protecting group.
    Type: Grant
    Filed: June 25, 1980
    Date of Patent: September 29, 1981
    Assignee: Merck & Co., Inc.
    Inventors: Thomas M. H. Liu, Robert A. Reamer, Ichiro Shinkai, Meyer Sletzinger
  • Cephalosporin compounds
    Patent number: 4292427
    Abstract: Alcohols are reacted with certain isocyanate compounds to produce the N-substituted carbamoyloxy derivatives which are cleaved to obtain the carbamate.
    Type: Grant
    Filed: December 13, 1979
    Date of Patent: September 29, 1981
    Assignee: Merck & Co., Inc.
    Inventors: Stephen Marburg, Janos Kollonitsch
  • Process for the preparation of thienamycin and intermediates
    Patent number: 4290947
    Abstract: Disclosed is a process for the total synthesis of thienamycin from L-aspartic acid via intermediate III: ##STR1## R=H, blocking group or salt cation.
    Type: Grant
    Filed: May 29, 1980
    Date of Patent: September 22, 1981
    Assignee: Merck & Co., Inc.
    Inventors: Burton G. Christensen, Ronald W. Ratcliffe, Thomas N. Salzman
  • Synthesis of thienamycin via (3SR, 4RS)-3-((RS)-1-acyloxyethyl)-2-oxo-4-azetidineacetate
    Patent number: 4287123
    Abstract: Disclosed is a process for the stereocontrolled total synthesis of thienamycin, which synthesis proceeds via intermediate II: ##STR1## wherein R is a readily removable carboxyl protecting group; and ##STR2## is a readily removable acyl group.
    Type: Grant
    Filed: January 14, 1980
    Date of Patent: September 1, 1981
    Assignee: Merck & Co., Inc.
    Inventors: Thomas M. H. Liu, David G. Melillo, Kenneth M. Ryan, Ichiro Shinkai, Meyer Sletzinger